KR920007972A - Method for producing carboxylic anhydride - Google Patents

Method for producing carboxylic anhydride Download PDF

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Publication number
KR920007972A
KR920007972A KR1019910017277A KR910017277A KR920007972A KR 920007972 A KR920007972 A KR 920007972A KR 1019910017277 A KR1019910017277 A KR 1019910017277A KR 910017277 A KR910017277 A KR 910017277A KR 920007972 A KR920007972 A KR 920007972A
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South Korea
Prior art keywords
iodide
dialkyl
catalyst
alkyl
process according
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KR1019910017277A
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Korean (ko)
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KR100213514B1 (en
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죠오지 비이버 로버트
앵거스 그리너 니일
제프레이 걸리버 데이비드
마이클 소렐 로버트
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케이쓰 워윅 덴비
비피 케미칼즈 리미티드
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/54—Preparation of carboxylic acid anhydrides
    • C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Furan Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Ultra Sonic Daignosis Equipment (AREA)
  • Glass Compositions (AREA)
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Abstract

The solubility and stability of rhodium catalysts in rhodium-catalysed carbonylation of alkyl esters or alkyl ethers under substantially anhydrous conditions to produce carboxylic acid anhydrides is improved by the use of co-promoters selected from the group: 1,3-dialkyl-4-methylimidazolium iodide; 1,3-dialkyl-4-ethylimidazolium iodide; 1,3-dialkyl-4-n-propylimidazolium iodide; 1,3-dialkyl-4-isopropylimidazolium iodide; 1,3-dialkyl-4-n-butylimidazolium iodide 1,3-dialkyl-4-sec-butylimidazolium iodide 1,3-dialkyl-4-tert-butylimidazolium iodide; 1,3-dialkyl-2,4,5-trimethylimidazolium iodide and mixtures thereof where the alkyl groups are independently C1 to C20 alkyl.

Description

카르복실산 무수물의 제조방법Method for producing carboxylic anhydride

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (11)

실질상 무수 조건하의 반응대에서 촉매, 요오다이드 조촉매 및 공-조촉매 존재하에 일산화탄소를 카르복실산 에스테르 또는 알킬 에테르와 반응시켜 카르복신산 무수물을 제조하는 방법에 있어서, 공-조촉매가 1,3-디알킬-4-메틸이미다졸륨 요오다이드, 1,3-디알킬-4-n-프로필이미다졸륨 요오다이드, 1,3-디알킬-4-이소프로필이미다졸륨 요오다이드, 1,3-디알킬-4-n-부틸이미다졸륨요오다이드, 1,3-4-sec-부틸이미다졸륨 요오다이드, 1,3-디알킬-2,4,5-트릴메틸이미다졸륨 요오다이드 및 그의 혼합물(여기서, 알킬기는 각각 C1~C20알킬이다)로 구성된 군에서 선택됨을 특징으로 하는 방법.In a process for producing carboxylic anhydride by reacting carbon monoxide with a carboxylic acid ester or an alkyl ether in the presence of a catalyst, iodide promoter and co-catalyst in a reaction zone under substantially anhydrous conditions, the co-catalyst is 1,3-dialkyl-4-methylimidazolium iodide, 1,3-dialkyl-4-n-propylimidazolium iodide, 1,3-dialkyl-4-isopropylimidazolium Iodide, 1,3-dialkyl-4-n-butylimidazolium iodide, 1,3-4-sec-butylimidazolium iodide, 1,3-dialkyl-2,4, 5-trimethylmethylimidazolium iodide and mixtures thereof, wherein the alkyl groups are each C 1 to C 20 alkyl. 제1항에 있어서, 공-조촉매의 알킬기가 메틸 또는 에틸인 방법.The method of claim 1 wherein the alkyl group of the co-catalyst is methyl or ethyl. 제1항에 있어서, 공-조촉매가 1,3,4-트리메틸이미다졸륨 요오다이드 및 1,2,3,4,5-펜타메틸이미다졸륨 요오다이드로 구성된 군에서 선택되는 방법.The method of claim 1, wherein the co-catalyst is selected from the group consisting of 1,3,4-trimethylimidazolium iodide and 1,2,3,4,5-pentamethylimidazolium iodide. 제1항 내지 제3항중 어느 한 항에 있어서, 공-조촉매가 상응하는 이미다졸을 알킬 요오다이드로 4분화함으로써 원위치에(in situ)제조되는 방법.The process according to claim 1, wherein the co-catalyst is prepared in situ by quaternizing the corresponding imidazole with alkyl iodide. 제4항에 있어서, 상응하는 이미다졸이 덜 치환된 이미다졸을 알킬 요오다이드로 알킬화함으로써 원위치로 제조되는 방법.The method of claim 4, wherein the corresponding imidazole is prepared in situ by alkylating less substituted imidazole with alkyl iodide. 제1항 내지 제5항중 어느 한항에 있어서, 로듐 촉매 및 조촉매를 반응대에 재순환하기 전에 반응대에서 연속적으로 반응매질을 제거하고 반응매질에서 카르복실산 무수물 생성물을 분리하여 조작되는 방법.The process according to any one of claims 1 to 5, which is operated by continuously removing the reaction medium in the reaction zone and separating the carboxylic anhydride product from the reaction medium before recycling the rhodium catalyst and the promoter to the reaction bed. 제1항 내지 제6항중 어느 한 항에 있어서, 카르복실산 에스테르 또는 알킬 에테르가 2~6개의 탄소원자를 갖는 방법.The process according to claim 1, wherein the carboxylic ester or alkyl ether has 2 to 6 carbon atoms. 제7항에 있어서, 카르복실산 에스테르가 메틸 아세테이트 또는 에틸 아세테이트인 방법.8. The method of claim 7, wherein the carboxylic acid ester is methyl acetate or ethyl acetate. 제1항 내지 제8항중 어느 한 항에 있어서, 소정량의 알칸올 및/또는 물이 카르복실산 에스테르 및/또는 알킬 에테르 피드스톡과 함께 반응대에 도입되어 카르복실산을 공생성하는 방법.The process according to claim 1, wherein a predetermined amount of alkanol and / or water is introduced into the reaction zone together with the carboxylic ester and / or alkyl ether feedstock to co-produce the carboxylic acid. 제9항에 있어서, 소정량의 메탄올 및/또는 물이 메틸 아세테이트와 함께 반응대에 도입되어 아세트산 및 아세트산 무수물을 공생성하는 방법.10. The process of claim 9, wherein a predetermined amount of methanol and / or water is introduced into the reaction zone with methyl acetate to co-produce acetic acid and acetic anhydride. 제1항 내지 제10항중 어느 한 항에 있어서, 공-조촉매가 로듐 촉매에 대한 몰비 0.5:1~105:1로 존재하는 방법.The process according to claim 1, wherein the co-catalyst is present in a molar ratio of 0.5: 1 to 10 5 : 1 relative to the rhodium catalyst. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019910017277A 1990-10-03 1991-10-02 Process for the production of carboxylic acid anhydrides KR100213514B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9021454.5 1990-10-03
GB909021454A GB9021454D0 (en) 1990-10-03 1990-10-03 Process

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KR920007972A true KR920007972A (en) 1992-05-27
KR100213514B1 KR100213514B1 (en) 1999-08-02

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US (1) US5298586A (en)
EP (1) EP0479463B1 (en)
JP (1) JPH04257538A (en)
KR (1) KR100213514B1 (en)
CN (1) CN1033698C (en)
AT (1) ATE131468T1 (en)
AU (1) AU634912B2 (en)
CA (1) CA2052632A1 (en)
CS (1) CS300491A3 (en)
DE (1) DE69115424T2 (en)
FI (1) FI914647A (en)
GB (1) GB9021454D0 (en)
HU (1) HUT59898A (en)
MX (1) MX9101414A (en)
MY (1) MY107657A (en)
NO (1) NO913860L (en)
NZ (1) NZ240009A (en)
SU (1) SU1834883A3 (en)
YU (1) YU161791A (en)
ZA (1) ZA917709B (en)

Families Citing this family (20)

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GB9120902D0 (en) * 1991-10-02 1991-11-13 Bp Chem Int Ltd Purification process
KR960007736B1 (en) * 1993-07-27 1996-06-11 한국과학기술연구원 Method of removing carbonyl compound in inlet gas
JPH06100479A (en) * 1992-06-30 1994-04-12 Korea Advanced Inst Of Sci Technol Simultaneous preparation of acetic acid, methyl acetate and acetic anhydride
GB9218346D0 (en) * 1992-08-28 1992-10-14 Bp Chem Int Ltd Process
GB9303770D0 (en) * 1993-02-25 1993-04-14 Bp Chem Int Ltd Process
GB9305902D0 (en) * 1993-03-22 1993-05-12 Bp Chem Int Ltd Process
DE10138778A1 (en) 2001-08-07 2003-02-20 Basf Ag Joint production of formic acid with a carboxylic (e.g. acetic) acid or derivatives, involves transesterifying a formic ester with a carboxylic acid, followed by carbonylation of the ester obtained
AU2003230306A1 (en) * 2002-05-06 2003-11-17 Eastman Chemical Company Continuous carbonylation process
DE10232305A1 (en) * 2002-07-17 2004-02-05 Goldschmidt Ag Process for the production of organomodified polysiloxanes using ionic liquids
DE10249928A1 (en) 2002-10-26 2004-05-06 Basf Ag Flexible process for the joint production of (i) formic acid, (ii) a carboxylic acid with at least two carbon atoms and / or its derivatives and (iii) a carboxylic acid anhydride
US7737298B2 (en) * 2006-06-09 2010-06-15 Eastman Chemical Company Production of acetic acid and mixtures of acetic acid and acetic anhydride
US7582792B2 (en) * 2006-06-15 2009-09-01 Eastman Chemical Company Carbonylation process
US7253304B1 (en) 2006-06-20 2007-08-07 Eastman Chemical Company Carbonylation process
US7629491B2 (en) * 2006-06-26 2009-12-08 Eastman Chemical Company Hydrocarboxylation process
US20090247783A1 (en) * 2008-04-01 2009-10-01 Eastman Chemical Company Carbonylation process
TW201022202A (en) * 2008-12-04 2010-06-16 China Petrochemical Dev Corp Method for producing carboxylic acid anhydride
TW201209034A (en) 2010-08-31 2012-03-01 China Petrochemical Dev Corp Production method for carboxylic acid anhydride
US9012683B2 (en) 2010-11-12 2015-04-21 Eastman Chemical Company Coproduction of acetic acid and acetic anhydride
CN115716780A (en) * 2014-06-20 2023-02-28 英力士乙酰英国有限公司 Process for the production of dimethyl ether from a gaseous mixture of carbon monoxide, hydrogen and methyl acetate
RU2680101C2 (en) * 2014-06-20 2019-02-15 Бп Кемикэлз Лимитед Method of purifying methyl acetate mixtures

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CA1058636A (en) * 1975-03-10 1979-07-17 Nabil Rizkalla Process for preparing carboxylic acid anhydrides
DE2836084A1 (en) * 1978-08-17 1980-03-06 Hoechst Ag METHOD FOR PRODUCING ACETIC ACID ANHYDRIDE
JPS6027651B2 (en) * 1981-08-13 1985-06-29 工業技術院長 Method for producing alkanpolyol
DE3144772A1 (en) * 1981-11-11 1983-05-19 Hoechst Ag, 6230 Frankfurt METHOD FOR PRODUCING ACETIC ACID ANHYDRIDE AND ACETIC ACID
NZ203226A (en) * 1982-02-13 1985-08-30 Bp Chemical Ltd Production of acetic anhydride from methanol and carbon monoxide
GB8404136D0 (en) * 1984-02-16 1984-03-21 Bp Chem Int Ltd Carbonylation process
CA1228867A (en) * 1984-05-03 1987-11-03 G. Paull Torrence Methanol carbonylation process
DE3429179A1 (en) * 1984-08-08 1986-02-20 Hoechst Ag, 6230 Frankfurt METHOD FOR THE SIMULTANEOUS PRODUCTION OF CARBONIC ACIDS AND CARBONIC ACID ANHYDRIDES AND IF ANY. CARBONIC ACID ESTERS
EP0391680B1 (en) * 1989-04-06 1994-06-15 BP Chemicals Limited Process for preparing carboxylic acids

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Publication number Publication date
CA2052632A1 (en) 1992-04-04
HUT59898A (en) 1992-07-28
NO913860D0 (en) 1991-10-02
EP0479463A3 (en) 1992-12-02
EP0479463A2 (en) 1992-04-08
NZ240009A (en) 1993-01-27
MX9101414A (en) 1994-06-30
JPH04257538A (en) 1992-09-11
AU8551091A (en) 1992-04-30
CN1033698C (en) 1997-01-01
EP0479463B1 (en) 1995-12-13
GB9021454D0 (en) 1990-11-14
ZA917709B (en) 1993-03-26
US5298586A (en) 1994-03-29
MY107657A (en) 1996-05-30
ATE131468T1 (en) 1995-12-15
AU634912B2 (en) 1993-03-04
NO913860L (en) 1992-04-06
HU913145D0 (en) 1992-01-28
FI914647A0 (en) 1991-10-03
CN1061401A (en) 1992-05-27
CS300491A3 (en) 1992-04-15
DE69115424T2 (en) 1996-05-02
KR100213514B1 (en) 1999-08-02
YU161791A (en) 1994-06-10
SU1834883A3 (en) 1993-08-15
DE69115424D1 (en) 1996-01-25
FI914647A (en) 1992-04-04

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